ESPYs Prediction Playbook: Matt's Trades & Fades
Prediction market trader and analyst Matt Schmitto explains his top ESPY Awards positions, and why he's shorting the Oklahoma City Thunder.
MLB All-Star festivities are over and the regular season won’t resume until Friday, but I’m gearing up for an unconventional sweat Wednesday night.
Two weeks ago Kalshi launched a full slate of ESPY markets, and I jumped in early. I was lucky to lock in some quick gains, but I still carry plenty of risk heading into tonight’s show.
As of Wednesday morning, the total trading volume across 23 ESPY awards—plus a mention market for Shane Gillis’ opening monologue—tops $300K, with $75K on Best Team and $50K on Best Men’s Basketball Player.
Most of my trading is over, but I expect overall volume to climb steadily right up to showtime.
Here’s how I’ve approached the event, along with the reasoning behind some of my biggest positions.
Disclaimer: This content is not intended as trading or financial advice. Traders should always do their own research before investing or trading on financial markets.
First things first (Know before you trade)
Before clicking ‘Yes’ or ‘No’, make sure you understand the three basics for every award show: Who votes? When do they vote? And by what criteria?
The answers will impact how you trade. In the case of the ESPYs, voting is a full-fledged fan affair that opened on June 26 and will close at 5 p.m. ET today. For more tidbits to get you ready, you can read my Ten Things to Know Before Trading the 2025 ESPYs.
As we’ve seen in previous awards that use a similar process, the “most deserving” nominee doesn’t always win.
Exhibit A: During the American Music Awards, Eminem upset Kendrick Lamar for Rap/Hip‑Hop Artist of the Year and Post Malone won Male Country Artist of the Year. Eminem traded as low as 1¢, the equivalent 99-to-1 odds!
So, yeah. Expect surprises, which we also saw play out during the summer’s BET Awards that used a hybrid voting process, weighing votes from fans and an academy.
I’m looking for similar curveballs tonight.
My core thesis: Short the Thunder & SGA
If the Oklahoma City Thunder have a big night, I have a bad one.
Fresh off an NBA title, the Thunder and superstar Shai Gilgeous‑Alexander (SGA) are favorites in three categories: Best Team 67¢ (67%); Best Athlete 63¢ (63%); Best Men’s Basketball Player 91¢ (91%).
I’m shorting all three.
With Oklahoma City victory and SGA’s MVP awards still on the minds of voters, recency bias is certainly in their favor — but possibly overpriced.
There some things working against the Thunder:
The NBA Finals stretched to a decisive Game 7 where the Thunder pulled away only after Tyrese Haliburton exited with a torn achilles.
Oklahoma City is a small market that doesn’t draw in fans from across the country like the Lakers and Celtics.
At least anecdotally, there’s anti-SGA sentiment due to his style of play as basketball fans dub him a “free throw merchant.”
It doesn’t hurt that there’s an entire state that hates the Thunder for sheer existence. (Chill, Supersonic fans. Kalshi says there’s a 27% chance that Seattle will get an NBA team before 2030.)
I have ‘No’ contracts on the Thunder in the Best Team market at an average of 30¢ (30%), along with ‘Yes’ shares spread across the Philadelphia Eagles 32¢ (32%), Florida Panthers 6¢ (6%) and USA Women’s National Soccer Team 12¢ (12%).
Jalen Hurts and the Eagles knocked off Patrick Mahomes and the one-loss Kansas City Chiefs, a team that most of the country despises too.
An NHL team has never won the award, yet I couldn’t help but buy the Panthers who are back-to-back Stanley Cup champions.
The USWNT, my favorite darkhorse, has won the award both times in which they were nominated; however, circumstances were different, with their ESPY wins coming on the heels of World Cup runs taking place much closer to the voting window than last year’s Paris Olympics.
Sure, the Thunder will probably win, but I think it’s closer to a coin flip against the field.
With all of that in mind, I shorted SGA winning Best Athlete, buying a hefty amount of ‘No’ contracts at 41¢ (41%) while adding ‘Yes’ contracts for Saquon Barkley 30¢ (30%) and Shohei Ohtani 15¢ (15%).
I stuck to my guns trading Best Basketball Player, too. SGA is the MVP, and again is likely to win the award, but I think there’s a greater than 10% chance that voters side with Nikola Jokic.
Note: If you’re trading Best Basketball Player, make sure to compare prices for both ‘Yes’ Nikola Jokic and ‘No’ Shai Gilgeous-Alexander; as of Wednesday morning, SGA’s ‘No’ at 10¢ (10%) is actually one cent cheaper than Jokic’s 11¢ (11%) which is an inefficiency.
Author’s Note: I plan to hold my current contracts through resolution, but keep in mind that I can absolutely profit from these prices moving in a certain direction. That’s not my intention, but unless you know me you shouldn’t trust me—something to keep in mind when reading other prediction market tips throughout the space.
More ESPY trades
Best Athlete With A Disability - When the market launched I knew not one of the four nominees, so I turned to social media accounts and google search trends, quickly landing on Ezra Frech ‘Yes’ at 55¢ (55%). Two gold medals in the 2024 Paris Paralympic Games versus one for Norma and none for Elliott or McFadden is icing on top.
Best Football Player - The last running back to win the award was Adrian Peterson in 2013. Having bought Saquon Barkley ‘No’ at 21¢ (21%), I’ll cross my fingers that the trend continues but I can’t say I’m confident.
Best College Athlete (Men’s) - Monitoring early prices, I bought Travis Hunter ‘Yes’ at 49¢ (49%), a bargain compared to his current price of 86¢ (86%). I have since hedged with Cooper Flagg ‘Yes’ contracts at 24¢ (24%). There are four nominees but this is a two-person race.
Shane Gillis will say… Drake 52¢ (52%), Epstein 20¢ (20%), and Diddy 24¢ (24%) during his opening monologue. I generally play the ‘No’ when trading mention markets, but c’mon, it’s Shane (and have you seen Drake’s new tattoo?)
